EP 85: Nobody Cares About Your Crappy Little Startup

2025-04-21

Building a business with purpose will push you to grow in ways you probably didn’t expect. What happens when your ambition outpaces your timing? Or when your team starts breaking down and you realize the real issue starts with you? In this episode, Alex Raymond talks with Brian Dally, the co-founder and CEO of Groundfloor, a fintech company that gives everyday investors access to real estate debt. Brian shares what he learned from starting too early, betting on the wrong timelines, and eventually paving the way for a market that wasn’t quite read...

In this episode, Alex Raymond talks with Brian Dally, the co-founder and CEO of Groundfloor, a fintech company that gives everyday investors access to real estate debt. Brian shares what he learned from starting too early, betting on the wrong timelines, and eventually paving the way for a market that wasn’t quite ready for him.

Brian also opens up about a turning point in his leadership when a blowout between two teams during a family ski trip forced him to confront the culture he had helped create. That moment led to a reset, not just in how the company operated, but in how he saw himself as a leader.

What do you do when your company hits a wall? How do you stay committed when the cost of building starts to feel personal? Brian reflects on his spiritual life, his leadership missteps, and the values that guide him today. He also shares the habits that keep him steady like hiking Colorado trails, practicing mindfulness, and checking in with the people who matter most.

If you’re building something ambitious, this conversation will make you think more deeply about the kind of person you’re becoming in the process.

Episode Breakdown:

00:00 Introduction

03:07 Early Challenges of Launching Groundfloor

05:55 The Cost of Being Early

08:10 Lessons from Republic Wireless

12:09 Personal Growth Through Leadership

14:45 Faith, Vulnerability, and Inner Work

16:48 How Company Culture Broke and Got Rebuilt

23:05 Big Goals, Ambition, and Opportunity Cost

30:59 Real-World Impact on Customers

34:02 Habits That Keep Brian Grounded